Cyclododecanone (K) and cyclododecanol (A) are intermediates in the production of nylon-12 and 1,12-dodecanedioic acid (DDDA). The air oxidation of cyclododecane produces a mixture containing K, A and a significant amount of cyclododecyl hydroperoxide (P). The P can be decomposed into more K and A. A boron compound may be used as a catalyst for the decomposition; see UK Patent No. 1,032,390.
U.S. Pat. No. 4,465,861 discloses a process for the conversion of cyclohexyl hydroperoxide to a mixture of cyclohexanone and cyclohexanol using, among others, a salt of chromium, such as chromium octoate, and a stabilizing agent. Cyclohexyl hydroperoxide can be made from the oxidation of cyclohexane. The oxidation results in a reaction mixture containing cyclohexanone, cyclohexanol, cyclohexyl hydroperoxide, unreacted cyclohexane, as well as some water and acids. Before the cyclohexyl hydroperoxide in this reaction mixture can be decomposed with a chromium catalyst to provide more cyclohexanone and cyclohexanol, the acids must be washed away with water, and substantially all the water--both that produced during cyclohexanone oxidation and that used to wash away the acids--must be removed. Typical cyclohexanone and cyclohexanol production from peroxide decomposition results in cyclohexanone to cyclohexanol ratios of about 3.
Because it is expensive to dispose of boron-containing waste from commercial operations, there is a need for a process for the conversion of cyclododecane to DDDA that does not use a boron compound to facilitate the decomposition of cyclododecyl hydroperoxide. There is also a need to decompose cyclododecyl hydroperoxide in a manner that results in a high ratio of K to A. Cyclododecanone (K) is a more valuable product than cyclododecanol (A): cyclododecanone can be converted to the corresponding lactam and ultimately to nylon-12, and cyclododecanone can also be used cost-efficiently to produce DDDA, since it is already partially oxidized from A. Finally, there is a need to be able to catalytically decompose cyclododecyl hydroperoxide without the need to wash away acids formed during cyclododecane oxidation and without the need to remove water.